1.0 2011-09-21 00:15:29 UTC 2015-07-21 06:57:15 UTC FDB022533 Diadenosine hexaphosphate Diadenosine hexaphosphate (AP6A) is a diadenosine polyphosphate. Diadenosine polyphosphates (APnAs, n = 3-6) are a family of endogenous vasoactive purine dinucleotides which have been isolated from thrombocytes. APnAs have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. APnAs isolated substances are AP3A, AP4A, AP5A, and AP6A. APnAs are naturally occurring substances that facilitate tear secretion; they are released from the corneal epithelium, they stimulate tear production and therefore they may be considered as physiological modulators of tear secretion. The APnAs were discovered in the mid-sixties in the course of studies on aminoacyl-tRNA synthetases (aaRS). APnAs have emerged as intracellular and extracellular signalling molecules implicated in the maintenance and regulation of vital cellular functions and become considered as second messengers. Great variety of physiological and pathological effects in mammalian cells was found to be associated with alterations of APnAs. APnAs are polyphosphated nucleotidic substances which are found in the CNS and are known to be released in a calcium-dependent manner from storage vesicles in brain synaptosomes. AP6A is an avid inhibitor of eosinophil-derived neurotoxin (EDN). EDN is a catalytically proficient member of the pancreatic ribonuclease superfamily secreted along with other eosinophil granule proteins during innate host defense responses and various eosinophil-related inflammatory and allergic diseases. The ribonucleolytic activity of EDN is central to its antiviral and neurotoxic activities and possibly to other facets of its biological activity. AP6A have been demonstrated to be involved in the control of vascular tone as well as the growth of vascular smooth muscle cells and hence, possibly, in atherogenesis. AP6A have been identified in human platelets and shown to be an important modulator of cardiovascular function. (PMID: 11212966, 12738682, 11810214, 9607303, 8922753, 16401072, 12738682, 10094777) [HMDB] Adenosine 5'-(heptahydrogen hexaate) P->5'-ester with adenosine Adenosine 5'-(heptahydrogen hexaate)5'-5'-ester with adenosine Adenosine 5'-(heptahydrogen hexaphosphate) P->5'-ester with adenosine Adenosine 5'-(heptahydrogen hexaphosphate)5'-5'-ester with adenosine Adenosine 5'-hexaate 5'-ester with adenosine Adenosine 5'-hexaic acid 5'-ester with adenosine Adenosine 5'-hexaphosphate 5'-ester with adenosine Adenosine-(5')-hexaO-(5')-adenosine Adenosine-(5')-hexaphospho-(5')-adenosine Ap(6)A AP6A AppppppA Diadenosine 5',5''''-P1,P6-hexaate Diadenosine 5',5''''-P1,P6-hexaic acid Diadenosine 5',5''''-P1,P6-hexaphosphate Diadenosine hexaate Diadenosine hexaic acid P1,P6-Di(adenosine-5')hexaate P1,P6-Di(adenosine-5')hexaic acid P1,P6-di(Adenosine-5')hexaphosphate C20H30N10O25P6 996.3468 995.980925632 {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid AppppppA 56983-23-4 NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1 InChI=1S/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1 PZCFFCOJNXGTIM-XPWFQUROSA-N belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. (5'->5')-dinucleotides Organic compounds Nucleosides, nucleotides, and analogues (5'->5')-dinucleotides Aromatic heteropolycyclic compounds 6-aminopurines Aminopyrimidines and derivatives Azacyclic compounds Glycosylamines Heteroaromatic compounds Hydrocarbon derivatives Imidolactams Monoalkyl phosphates Monosaccharide phosphates N-substituted imidazoles Organic oxides Organopnictogen compounds Oxacyclic compounds Pentose phosphates Primary amines Purine nucleotide sugars Purine ribonucleoside monophosphates Purine ribonucleoside polyphosphates Secondary alcohols Tetrahydrofurans (5'->5')-dinucleotide 6-aminopurine Alcohol Alkyl phosphate Amine Aminopyrimidine Aromatic heteropolycyclic compound Azacycle Azole Glycosyl compound Heteroaromatic compound Hydrocarbon derivative Imidazole Imidazopyrimidine Imidolactam Monoalkyl phosphate Monosaccharide Monosaccharide phosphate N-glycosyl compound N-substituted imidazole Organic nitrogen compound Organic oxide Organic oxygen compound Organic phosphoric acid derivative Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Oxacycle Pentose phosphate Pentose-5-phosphate Phosphoric acid ester Primary amine Purine Purine nucleotide sugar Purine ribonucleoside monophosphate Purine ribonucleoside polyphosphate Pyrimidine Secondary alcohol Tetrahydrofuran diadenosyl hexaphosphate Solid logp 0.26 ALOGPS logs -2.15 ALOGPS solubility 6.99e+00 g/l ALOGPS logp -10 ChemAxon pka_strongest_acidic 0.28 ChemAxon pka_strongest_basic 5.3 ChemAxon iupac {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid ChemAxon average_mass 996.3468 ChemAxon mono_mass 995.980925632 ChemAxon smiles NC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1 ChemAxon formula C20H30N10O25P6 ChemAxon inchi InChI=1S/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1 ChemAxon inchikey PZCFFCOJNXGTIM-XPWFQUROSA-N ChemAxon polar_surface_area 527.03 ChemAxon refractivity 187.85 ChemAxon polarizability 76.38 ChemAxon rotatable_bond_count 18 ChemAxon acceptor_count 26 ChemAxon donor_count 12 ChemAxon physiological_charge -6 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 25322 Specdb::MsMs 25323 Specdb::MsMs 25324 Specdb::MsMs 31880 Specdb::MsMs 31881 Specdb::MsMs 31882 Specdb::MsMs 2421213 Specdb::MsMs 2421214 Specdb::MsMs 2421215 Specdb::MsMs 2544814 Specdb::MsMs 2544815 Specdb::MsMs 2544816 Specdb::NmrOneD 9102 Specdb::NmrOneD 9103 Specdb::NmrOneD 9104 Specdb::NmrOneD 9105 Specdb::NmrOneD 9106 Specdb::NmrOneD 9107 Specdb::NmrOneD 9108 Specdb::NmrOneD 9109 Specdb::NmrOneD 9110 Specdb::NmrOneD 9111 Specdb::NmrOneD 9112 Specdb::NmrOneD 9113 Specdb::NmrOneD 9114 Specdb::NmrOneD 9115 Specdb::NmrOneD 9116 Specdb::NmrOneD 9117 Specdb::NmrOneD 9118 Specdb::NmrOneD 9119 Specdb::NmrOneD 9120 Specdb::NmrOneD 9121 HMDB01282 B6P #<Reference:0x000055ce31bd3c88> #<Reference:0x000055ce31bd3ad0> #<Reference:0x000055ce31bd3918> #<Reference:0x000055ce31bd3738> #<Reference:0x000055ce31bd3558> #<Reference:0x000055ce31bd33a0> #<Reference:0x000055ce31bd31e8> #<Reference:0x000055ce31bd3030> #<Reference:0x000055ce31bd2e78> #<Reference:0x000055ce31bd2cc0> #<Reference:0x000055ce31bd2b08> #<Reference:0x000055ce31bd2950> #<Reference:0x000055ce31bd2798> #<Reference:0x000055ce31bd25e0> #<Reference:0x000055ce31bd2428> #<Reference:0x000055ce31bd2270> #<Reference:0x000055ce31bd20b8> #<Reference:0x000055ce31bd1f00> #<Reference:0x000055ce31bd1d48> #<Reference:0x000055ce31bd1b90> #<Reference:0x000055ce31bd19d8> #<Reference:0x000055ce31bd1820> #<Reference:0x000055ce31bd1668> #<Reference:0x000055ce31bd14b0> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823